CARBIDOPA ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H14N2O4
Molecular Weight	226.2292
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@](CC1=CC(O)=C(O)C=C1)(NN)C(O)=O

InChI

InChIKey=TZFNLOMSOLWIDK-JTQLQIEISA-N

InChI=1S/C10H14N2O4/c1-10(12-11,9(15)16)5-6-2-3-7(13)8(14)4-6/h2-4,12-14H,5,11H2,1H3,(H,15,16)/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H14N2O4
Molecular Weight	226.2292
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017830s014s016s017s018s019s030lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10934669

Carbidopa is a competitive inhibitor of aromatic L-amino acid decarboxylase that does not cross the blood-brain barrier, is routinely administered with levodopa (LD) for the treatment of the symptoms of idiopathic Parkinson’s disease (paralysis agitans), postencephalitic parkinsonism, and symptomatic parkinsonism, which may follow injury to the nervous system by carbon monoxide intoxication and/or manganese intoxication. Current evidence indicates that symptoms of Parkinson’s disease are related to depletion of dopamine in the corpus striatum. Administration of dopamine is ineffective in the treatment of Parkinson’s disease apparently because it does not cross the blood-brain barrier. However, levodopa, the metabolic precursor of dopamine, does cross the blood- brain barrier, and presumably is converted to dopamine in the brain. When levodopa is administered orally it is rapidly decarboxylated to dopamine in extracerebral tissues so that only a small portion of a given dose is transported unchanged to the central nervous system. For this reason, large doses of levodopa are required for adequate therapeutic effect and these may often be accompanied by nausea and other adverse reactions, some of which are attributable to dopamine formed in extracerebral tissues. Carbidopa inhibits decarboxylation of peripheral levodopa. Carbidopa has not been demonstrated to have any overt pharmacodynamic actions in the recommended doses.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DOPA decarboxylase 15 Target ID: CHEMBL1843 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11106255	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Idiopathic Parkinson's disease 19 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017830s014s016s017s018s019s030lbl.pdf	Palliative		Approved 8583	LODOSYN Approved Use LODOSYN is indicated for use with carbidopa-levodopa or with levodopa in the treatment of the symptoms of idiopathic Parkinson’s disease (paralysis agitans), postencephalitic parkinsonism, and symptomatic parkinsonism, which may follow injury to the nervous system by carbon monoxide intoxication and/or manganese intoxication. LODOSYN is for use with carbidopa-levodopa in patients for whom the dosage of carbidopa-levodopa provides less than adequate daily dosage (usually 70 mg daily) of carbidopa. LODOSYN is for use with levodopa in the occasional patient whose dosage requirement of carbidopa and levodopa necessitates separate titration of each medication. LODOSYN is used with carbidopa-levodopa or with levodopa to permit the administration of lower doses of levodopa with reduced nausea and vomiting, more rapid dosage titration, and with a somewhat smoother response. However, patients with markedly irregular (“on-off”) responses to levodopa have not been shown to benefit from the addition of carbidopa. Since carbidopa prevents the reversal of levodopa effects caused by pyridoxine, supplemental pyridoxine (vitamin B6), can be given to patients when they are receiving carbidopa and levodopa concomitantly or as carbidopa-levodopa. Launch Date 1977

C_max

Value	Dose	Co-administered	Analyte	Population
108.57 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30295551	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA	LEVODOPA	CARBIDOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
559.92 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30295551	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA	LEVODOPA	CARBIDOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.09 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30295551	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA	LEVODOPA	CARBIDOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
64% DRUG LABEL https://www.drugs.com/monograph/levodopa-carbidopa.html			CARBIDOPA plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 550 CYP2C19 2057 MRP4 290 MRP3 246 CYP1A2 2153 MRP2 499 P-gp 1741 BCRP 910 CYP19A1 429 CYP2A6 879 CYP2E1 1060 UMAT 30		CYP1B1 71 CYP1A2 832 CYP1A1 151

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=225144194	inconclusive [IC50 11.9877 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=225144194	inconclusive [IC50 30.1116 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/410#sid=11113507	inconclusive [IC50 7.943 uM]
CYP2A6 911	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625246#sid=103770731	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625250#sid=103770731	no [IC50 >10 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1325#sid=8139862	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144204461	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/899#sid=11113507	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/891#sid=11113507	no
MRP1 232	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/799#sid=8139862	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1326#sid=8139862	no
UMAT 30	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/602162#sid=93576631	no
AHR 9	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/28963435/	yes
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/28963435/	yes
CYP1A2 2333	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/28963435/	yes
CYP1B1 93	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/28963435/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/588834#sid=50104417

PubMed

Title	Date	PubMed
Centrally mediated increased reflex vagal bradycardia after L-dopa in monoamine oxidase-inhibited anesthetized dogs.	1976 Feb	1255483
Chronic akinetic mutism after mesencephalic-diencephalic infarction: remediated with dopaminergic medications.	2001	11811256
Benserazide decreases central AADC activity, extracellular dopamine levels and levodopa decarboxylation in striatum of the rat.	2001	11459076
Catechol-O-methyltransferase inhibitors in the management of Parkinson's disease.	2001	11346021
Levodopa induces dyskinesias in normal squirrel monkeys.	2001 Aug	11506410
L-dopa induces dyskinesia in normal monkeys: behavioural and pharmacokinetic observations.	2001 Aug	11498717
L-DOPA and glia-conditioned medium have additive effects on tyrosine hydroxylase expression in human catecholamine-rich neuroblastoma NB69 cells.	2001 Aug	11483656
Amantadine for dyskinesia in patients affected by severe Parkinson's disease.	2001 Feb	11487209
Case report: successful use of rectally administered levodopa-carbidopa.	2001 Jan	11212422
Aldrin-induced locomotor activity: possible involvement of the central GABAergic-cholinergic-dopaminergic interaction.	2001 Jan-Feb	11785907
Amelioration of frozen gait by tandospirone, a serotonin 1A agonist, in a patient with pure akinesia developing resistance to L-threo-3,4-dihydroxyphenylserine.	2001 Jul-Aug	11479395
A novel neurodevelopmental syndrome responsive to 5-hydroxytryptophan and carbidopa.	2001 Jun	11386854
Molecular analysis and long-term follow-up of patients with different forms of 6-pyruvoyl-tetrahydropterin synthase deficiency.	2001 May	11388593
Structural insight into Parkinson's disease treatment from drug-inhibited DOPA decarboxylase.	2001 Nov	11685243
Dopamine mediates striatal malonate toxicity via dopamine transporter-dependent generation of reactive oxygen species and D2 but not D1 receptor activation.	2001 Oct	11595758
Post-stroke violent adventitial movement responsive to levo-dopa/carbi-dopa therapy.	2001 Oct	11595087
Dopaminergic therapy with carbidopa L-dopa for left neglect after stroke: a case series.	2001 Sep	11552204
Stereoselective effect of (R)- and (S)-1-methyl-1,2,3,4-tetrahydroisoquinolines on a mouse model of Parkinson's disease.	2001 Sep 1	11604249
Atypical presentation of dopa-responsive dystonia: generalized hypotonia and proximal weakness.	2001 Sep 25	11571350
Clinical management of neuroleptic malignant syndrome.	2001 Winter	11525080
[Neuroleptic malignant syndrome].	2002	12474710
Chronic high dose L-DOPA alone or in combination with the COMT inhibitor entacapone does not increase oxidative damage or impair the function of the nigro-striatal pathway in normal cynomologus monkeys.	2002	11793162
[Serotonin syndrome: report of a fatal case and review of the literature].	2002 Apr	12003730
Two advances in the management of Parkinson disease.	2002 Aug	12184472
Semicarbazide-sensitive amine oxidase (SSAO) gene expression in alloxan-induced diabetes in mice.	2002 Dec	12606817
Levodopa-carbidopa with occlusion in older children with amblyopia.	2002 Dec	12506278
Effect of promoters on cellular immune response induced by recombinant fowlpox virus expressing multi-epitope polypeptides from HIV-1.	2002 Dec	12452800
Screening for tetrahydrobiopterin deficiency among hyperphenylalaninemia patients in Southern China.	2002 Feb	11940335
[Benefit of L-DOPA-without-DCI (decarboxylase inhibitor) therapy on wearing-off phenomenon in advanced stages of Parkinson's disease patients].	2002 Feb	11889758
Parkinson disease neuropathology: later-developing dementia and loss of the levodopa response.	2002 Jan	11790237
Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice.	2002 Jan-Feb	11980384
In vivo metabolism and partitioning of 6-[18F]fluoro-L-meta-tyrosine in whole blood: a unified compartment model.	2002 Jun 7	12108778
Parkinsonism associated with interferon alpha therapy for chronic myelogenous leukemia.	2002 Mar	11965836
Bruxism as presenting feature of Parkinson's disease.	2002 Mar	11922248
Entacapone in restless legs syndrome.	2002 Mar	11921139
Influence of layer position on in vitro and in vivo release of levodopa methyl ester and carbidopa from three-layer matrix tablets.	2002 Mar	11880007
[Hallucinations caused by paroxetine taken together with a levodopa-carbidopa preparation].	2002 Mar 23	11938583
Dopaminergic transmission in the rat striatum in vivo in conditions of pharmacological modulation.	2002 Mar-Apr	11942697
Effect of levodopa and carbidopa in human amblyopia.	2002 Mar-Apr	11911549
Levodopa plus carbidopa before physiotherapy increased motor recovery after stroke.	2002 Mar-Apr	11874277
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics.	2002 May 14	12011296
Role of sphingosine synthesis inhibition in transcutaneous delivery of levodopa.	2002 May 15	11996809
Simultaneous determination of dopa and carbidopa enantiomers by capillary zone electrophoresis.	2002 Sep	12373770
Quantitative description of loss of clinical benefit following withdrawal of levodopa-carbidopa and bromocriptine in early Parkinson's disease.	2002 Sep	12360545
Olanzapine: a proarrhythmic drug?	2002 Sep	12355682
Leg muscle strength is reduced in Parkinson's disease and relates to the ability to rise from a chair.	2003 Feb	12539208
Reversal of parkinsonism following liver transplantation.	2003 Feb 11	12578945
Novel levodopa gastroretentive dosage form: in-vivo evaluation in dogs.	2003 Feb 14	12586509
Neonatal dopa-responsive extrapyramidal syndrome in twins with recessive GTPCH deficiency.	2003 Jan 28	12552057
Effect of pulsatile administration of levodopa on dyskinesia induction in drug-naïve MPTP-treated common marmosets: effect of dose, frequency of administration, and brain exposure.	2003 May	12722161

Patents

Sample Use Guides

In Vivo Use Guide

Whether given with carbidopa-levodopa or with levodopa, the optimal daily dose of LODOSYN (CARBIDOPA tablets) must be determined by careful titration. Most patients respond to a 1:10 proportion of carbidopa and levodopa, provided the daily dosage of carbidopa is 70 mg or more a day. The maximum daily dosage of carbidopa should not exceed 200 mg, since clinical experience with larger dosages is limited. If the patient is taking carbidopa-levodopa, the amount of carbidopa in carbidopa-levodopa should be considered when calculating the total amount of LODOSYN to be administered each day.

Route of Administration: Oral

In Vitro Use Guide

It was evaluated the effect of carbidopa on 6-18F-fluoro-3,4-dihydroxy-l-phenylalanine (18F-FDOPA) uptake in the murine β-cell line RIN-m5F. Incubation of RIN-m5F cells with 80 μM carbidopa did not significantly affect the cellular accumulation of 18F-FDOPA.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:56:05 GMT 2025` Edited by `admin` on `Mon Mar 31 17:56:05 GMT 2025`
Record UNII	KR87B45RGH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARBIDOPA ANHYDROUS

Common Name

English

BENZENEPROPANOIC ACID, .ALPHA.-HYDRAZINO-3,4-DIHYDROXY-.ALPHA.-METHYL-, (S)-

Preferred Name

English

carbidopa [INN]

Common Name

English

Carbidopa [WHO-DD]

Common Name

English

CARBIDOPA, L- ANHYDROUS

Common Name

English

CARBIDOPA ANHYDROUS [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C38149